Dyes tabularly arranged under each intermediate, with statistical and

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D Y ES C L A S S I F I EI
BY I N T E R M E D I A T E!
Dyes tabularly arranged under each
intermediate, with statistical and other
data for both dyes and intermediates.
Glossary of Dye and Intermediate
names alphabetically arranged.
BY
R. XORRIS SHREVE
Consulting Chemist
EN" COLLABORATION WITH
WARREN N. WATSON
AND
A. R. WILLIS
Chemists, U. S. Tariff Commission
BOOK DEPARTMENT
The CHEMICAL CATALOG CCttBPANY, Inc.
ONE MADISON AVKNUJS, NEW YORK, TJ. 8. A.
COPYRIGHT, 1922, BY
The CHEMICAL CATALOG COMPANY, Inc.
All Rights Reserved
Press of
J. J. Little & Ives Company
New York, U. S. A.
TABLE OF CONTEXTS
PAGE
PREFACE 3
ABBREVIATION'S 5
INTRODUCTION 7
PART I. INTERMEDIATES AND DYE TABLES . .. 17
KEY TO PART I 18
INTERMEDIATES WITH DYE TABLES. THE ARRANGEMENT OF INTER-
MEDL^TE NAMES 15 ALPHABETICAL AND INCLUDES CHEMICAL AND
COMMON OR TRIVIAL- NAMES 19
FORMULA INDEX OF INTERMEDIATES 581
PAET II. DYE NAMES 587
GLOSSARY OF DYE NAMES 589
PAGE INDEX OF SCHULTZ NUMBERS FOR DYES 625
PREFACE
Experience in the manufacture of dyes indicates that the proper
viewpoint for a correct technical program is from the intermediate side.
This is a direct corollary of the fact that the intermediates are the
materials out of which dyes are fabricated. Furthermore, the tremen-
dous complexity of the dye industry, the interrelationship of one dye to
another or of one intermediate to another, as well as the relationship of
dyes and intermediates to the whole organic chemical industry, all
require that there be available tables showing the commercial dyes
derived from each important intermediate. To give this is the prime
object of this work.
It is believed that this book will be of service not only to manufac-
turers in looking for uses of any intermediate, but to research chemists
and to students. Since the tables give the various outlets and the
poundage imported and manufactured, the book will aid the merchant
in the buying or selling of dyes and intermediates. The very com-
plete glossary of names, both of dyes and intermediates, will help in
many directions, especially as the intermediate part includes the
so-called common or trivial names. This feature will be of great
service in reading the older literature and patents.
The intermediate names are alphabetically arranged. Under each
principal name is given the synonyms, which are also cross-indexed in
their alphabetical order. A special feature is the giving of the name
used by Chemical Abstracts; this, together with the listing of the prin-
cipal formulas, will aid in the use of the Chemical Abstracts by the Dye
Chemist.
A Formula Index to the names of the intermediates and to the pages
is given following the main part of this book containing the alphabetical
treatment of the intermediates. Here the formulas of the intermediates
are listed in an alphabetical order as in a dictionary, except that CH
comes first; and in this way a 5-atom formula may precede a 3-atom
one. This is similar to the excellent formula index of the 1920 Chemical
Abstracts.
After the writer had been engaged for some time in the preparation
of this book, he was informed of a somewhat similar classification
undertaken by Messrs. Warren N. Watson and A. R. Willis of the
Tariff Commission, Washington, D.C. It was deemed fair to cooper-
Z
4 PREFACE
ate and to associate the two works by the mutual use of the other names
as " collaborators/7 Messrs. Watson and Willis have published a part
of their work, comprising about a third of the Schultz dyes, in the
Color Trade Journal serially from May to September during 1921.
This serial publication by Messrs. Watson and Willis and this book by
the writer are separate and independent productions. The writer,
however, takes this occasion to express his appreciation for advice and
help to Messrs. Watson and Willis.
It is a pleasure to acknowledge help from Dr. Austin M. Patterson
on the Chemical Abstracts nomenclature. Aid has also been rendered
by J. R. Minevitch, M. N. Conklin and Oscar Newman. The statistical
data are taken from the yearly Census of Dyes and Coal Tar Chemicals
compiled by the U. S. Tariff Commission, and from Artificial Dyestuffs
Used in the United States by Thomas H. Norton.
R. NORKIS SHREVE.
NEW YORK CITY
December, 1921.
ABBREVIATIONS
Dye Application Column
A Acid dye
ACr Acid chrome dye
B Basic dye
CL Color lake
D Direct dye
MF Color made on fiber
M Mordant dye
S Sulfur dye
ss Spirit soluble dye
V Vat dye
Statistics Column
I '14 Imports, Fiscal Year 1914 (year ending
June 30, 1914)
I '20 Imports, Calendar Year 1920
M717
M'18 Manufactured in Calendar Year
M'19 1917, 1918, 1919, or 1920
M'20
Literature References
BARNETT, ANTHRACENE AND ANTURAQUINONE
E. de Barry Barnctt, Anthracene and Anthraquinone, 1921.
D. Van Nostrand & Co.
BEIL.
Beilstcin, Handbuch clcr organischen Chemie (3rd Ed.).
BER.
Berichte dcr Deutschen Chcmischen Gesellschaft.
CAIN, INTERMEDIATE PRODUCTS
J. C. Cain, The Manufacture of Intermediate Products for Dyes,
Second Edition 1919, Macmillan & Co.
FRDL.
P. Friedlacnder, Fortschritte dcr Teerfarbcnfabrikation, 1877-1916,
12 vols., Julius Springer.
5
6 ABBREVIATIONS
GREEN, ORGANIC COLORING MATTERS
A. G. Green, A Systematic Survey of the Organic Colouring Matters,
1908 Edition, Macmillan & Co.
GEORGIEVICS AND GRANDMOUGIN, DYE CHEMISTRY
G. von Georgievics and E. Grandmougin, translated by F. A.
Mason. A Textbook of Dye Chemistry, 1920. Scott Green-
wood & Son.
HEUMANN, ANILINFARBEN
K. Heumann (Fourth part edited by G. Schultz), Die Anilinfarben
und ihre Fabrikation, Four Parts, 1888-1906, Friedrich Viewig.
LANGE, SCHWEPELFARBSTOFFE
Otto Lange, Die Schwefelfarbstoffe, ihre Herstellung und Verwen-
dung, 1912, Otto Spamer.
LANGE, ZWISCHENPRODTJKTE
Otto Lange, Die Zwischenprodukte der Teerfarbenfabrikation,
1920, Otto Spamer.
THORPE, Die. CHEMISTRY
Edw. Thorpe, A Dictionary of Applied Chemistry, First Edition,
Longmans Green & Co.
ULLMANN, ENZY. TECH. CHEMIE
Enzyklopaedie der technischen Chemie, Edited by Dr. Fritz Ull-
rnann, 1914. Urban & Schwarzenberg.
Miscellaneous
o ortho
m meta
p para
a alpha
/3 beta
N Nitrogen (signifies nitrogen attachment
of radical)
C. A. nomen. . . Chemical Abstracts nomenclature
(mols) Molecules
Schultz Number . Number for dye as given in Schultz,
Farbstofftabellen, 1914 Edition.
INTRODUCTION
The contents of this book fall into two parts: first, an alphabetical
list of intermediates with their data and dye tables, and second, an
aphabetical list of dye names referring to their Schultz numbers when
known, by which any dye here classified can be found in the tables by
looking in the "Page Index of Schultz Numbers" at the end of the book
for the appropriate pages.
Often an intermediate is known by as many as half a dozen names,
and each one is listed in its alphabetical order, but the synonyms all
refer to one name under which are arranged the tables and other data.
Thus the book is a glossary of intermediate names. In selecting the
name given at the head of the data for a certain intermediate, the
writer was influenced first by considerations of clearness and then
of custom and usage. For a full discussion of this important nomen-
clature question, reference is made to the nomenclature section of this
introduction.
Following the synonyms, is given the structural formula, the empirical
formula, and the molecular weight. It is the emphatic opinion of the
writer that the indexing of organic compounds by their formulas is the
simplest, the most universal, and the clearest. Chemical Abstracts,
starting with 1920, has inserted a formula index, and it is believed that
chemists can find a given intermediate quicker and more surely in
Chemical Abstracts by the use of this formula index than by the ordinary
subject index. The formulas given here will be an aid in this direction.
Furthermore a formula index is included in this book.
Under each intermediate there is listed a short description of methods
of Formation followed by Literature References. These are not exhaustive
in any sense, but the aim has been to give the usual commercial prepa-
ration together with several references to the literature for any one who
desires more details. The references to Lange, Zwischcnproduklo,
cover the German patents.
In order to give some basis for judging the extent to which a dye or
an intermediate is used, the statistical data for importation and manu-
facture in the United States is given under Statistics, These data are
taken from the following government reports: Census of Dyes and Coal-
Tar Chemicals, by U. S. Tariff Commission; Artificial Dyestujfs Used in
the U. S. by Thomas H. Norton, and Chemicals and Allied Products
9
7
8 INTRODUCTION
Used in the U. S. by E. R. Pickrell. The Imports 1914 both under inter-
mediates and under dyes refer to the imports for the fiscal year ending
June 30, 1914. Otherwise the imports, and always the amounts manu-
factured, refer to the calendar year marked. It is believed that the
addition of these statistical data to the tables will be of much service in
pointing out forcibly the relative commercial importance of the dyes
and intermediates, and will help to complete development of the dye
industry in America. In considering these statistics, it must be borne
in mind that since 1914 the United States has been endeavoring to
fully supply her own needs, and proceeded naturally along the lines of
least resistance, so that often a dye was manufactured because of its
comparative simplicity, to be later superseded by a more suitable dye
of more complexity. The Imports for 1914 (fiscal year ending June
30, 1914) are "normal" except that Vat Dyes were not imported as
heavily that year as had been the usual case.
The statistics of import of a dye, especially for the fiscal year ending
June 30, 1914, often include a number of very similar though not
identical dyes. These statistics were obtained by adding together the
individual dye weights as listed by Norton under a given Schultz
number.
Where Tlh M'19, Manufactured 1919, etc., are given followed by a
question mark, it indicates that the dye or intermediate was imported
or manufactured for the year marked but in amounts that have not
been disclosed by the U. S. Government.
When a figure is given for imports or manufactures of dyes or inter-
mediates, this figure always refers to pounds.
The tables proper give for any intermediate all the dyes listed in
Schultz, Farbstofftabellen, 1914 Edition, that are derived from this
intermediate. This includes practically all of the important dyes
except a few of the newer ones of undisclosed constitution. Thus a
given dye is separately arranged under each of its intermediates. As
there is named in a special column the Other Intermediates constituting
a dye besides the one at the head of each table, the intermediate rela-
tionship is clearly stated.
The following dyes listed in Schultz, Farbstofftabellen (1914), are
not classified, on account of lack of information as to their composition-
30 Radial Yellow G 706 Cachou de Laval
87 Peri Wool Blue 707 Sulfine Brown
608 Euchrysine 708 Sulfaniline Brown
609 Homophosphine G 744 Sulfo Black B, 2B
INTRODUCTION 0
751 Krygene Brown RB 756 Kryogene Black TGO
752 Kryogene Direct Blue GO 757 Sulfogcnc Brown G, D
753 Kryogene Direct Blue B 863 Anthraquinone Blue Green B XO
754 Kryogene Direct Blue 3B 871 Indanthrcne Violet RN Extra
755 Kryogene Black BNX
In very many cases, the writer has supplemented the information
in Schultz, Farbstofflabellen, as to composition of dyes, and hence has
been able to classify many dyes whose composition is indefinite in this
book. In a number of instances when Schultz refers the dyes to com-
plex intermediates, these have been split into simpler components, and
the components as well as the complex parent compound have all been
indexed. Also certain obvious errors in Schultz, Farbstofftabcllen, have
been corrected, as for example, where in //182, reference is made to
L-amino-4-naphthol-sulfonic acids which the patent refers to ar.a-r
sulfonic acids (l-amino-8-naphthol-sulfonic acids) and specifically names
H acid in the example given.
When the patents describing a dye list a number of intermediates,
then those listed under Example I of the patent are chosen for classifica-
tion unless, of course, Schultz, Farbstofftabdlen, gives definite composi-
tion to the dye. Quite often intermediates arc indexed even though
not a component part of the final dye, provided they were necessary
to its manufacture, e.g. benzoic acid in the manufacture of certain of
the Triphenyl-methane Dyes as Diphenylamine Blue and Aniline Blue.
All possible intermediates for any given dye are not indexed, but it
is hoped to extend the present classification at a later date. Previous
tables resembling those given here, but along much less extensive lines,
are to be found in Heumann, Die Anilinfarben und ihre Fabrication
IV, II, 2, pages 1943-2013, and Lefevre, Traite des Matures Coloranlca
(1896), pages 140-407.
In the column in the tables headed Other Intermediates Used and
Notes, there is given first the intermediates other than the one at the
head of the table, which compose the dye in question. Unless other-
wise marked, it is to be understood that one molecule of an intermediate
is used. When more than one molecule is employed, of the intermediate
heading the table, then the name of this intermediate is also given in
the Other Intermediates column followed by the number of molecules
(mols) that are used in the dye.
The notes are in brackets, and are mostly self-explanatory, and refer
chiefly to constituents, such as sulfur (S), sodium sulfide (Na S), and
2
the like, which enter into the formation of the dye. Such steps op